Real Woodstock is about spending the holiday season with family and friends in one of the prettiest Christmas-towns anywhere.

From gift shopping to cutting down your family Christmas tree, there is no better place to experience the magic and charm of holidays than in Real Woodstock.

While you're here, grab a bite to eat on or off the historic Woodstock Square. Shop for unique artisan gifts and delicious holiday treats at one of our many boutiques. See a live holiday performance at the beautiful Woodstock Opera House. Or take a free horse-drawn carriage ride around the cobblestoned Square under thousands of twinkling lights.

The Winter Solstice exhibition and Clayworkers’ Guild Holiday Sale is a one-stop shop for all your holiday needs! This year, the gallery showcases 2-D as well as 3-D artwork, fiber arts, ornaments, irresistible jewelry and all kinds of clever, shiny, offbeat objects with which to stuff stockings and celebrate a season of giving.

The Clayworkers' Guild of Illinois is an organization of craftsmen and artists who use clay as an expressive medium. The Guild strives to aid, encourage, advise and work together to support each other's endeavors.

Join us for our annual Pet Pictures with Santa! In addition to Santa and his elves visiting to take pictures with your pets, you will have the opportunity to make clay paw print ornaments as well! This is a great way to create a lasting keepsake featuring your pet's paw print for $10 each.

This year proceeds benefit Boxer Rebound & Helping Paws Animal Shelter. Cash or Check only. Through the holiday season we will also have a donation box for the animals at Helping Paws. Follow the link below for the list of items the shelter needs and for more on this event.

Friends and family gather on the historic Woodstock Square to kick-off the holiday season at Lighting of the Square, the day after Thanksgiving. At 7pm, a giant switch will be flipped as tens of thousands of twinkling lights illuminate the Woodstock sky. Come early and stay late for children’s activities, caroling, holiday shopping, Santa sightings, the Christmas Tree Walk at the Woodstock Opera House and Gingerbread House Walk at the Old McHenry County Courthouse. The Woodstock holiday season continues the next day with shopping for unique artisan gifts during Small Business Saturday and magical holiday events throughout the season!

Starting Friday, November 23, visit Woodstock's Oney’s Tree Farm, Moehling Christmas Tree Farm or Grandpa’s Christmas Tree Farm to get your family’s tree! Make a day in Woodstock and visit the charming Woodstock Square before for a meal or shopping for unique gifts at one of our many boutiques.

Get the whole family into the Christmas spirit to join Ebenezer Scrooge as he journeys through the Christmases of Past, Present and Future with his three Ghostly Guides. The production – with enchanting children, colorful costumes, clever special effects and merry Christmas carols – transports you to 1843 London. Capture the spirit of the holiday season with this classic Dickens tale.

If you are looking for unique artisan holiday gifts and festive treats for friends and family this season, there is no better place than Woodstock and the businesses on the charming Woodstock Square. Start

Check items off your holiday shopping list on Small Business Saturday, November 24 with local business owners in Woodstock and throughout McHenry County.

Free horse-drawn carriage rides around the cobblestone-lined Woodstock Square will be offered on Small Business Saturday outside the Woodstock Opera House and will continue until December 23 on Fridays, Saturdays and Sundays.

Go back in time and take a free ride around the Historic Woodstock Square during November and December on Fridays, Saturdays and Sundays. Free horse-drawn carriage rides around the cobblestone-lined Woodstock Square will be offered beginning on Small Business Saturday outside the Woodstock Opera House and will continue until December 23.

If you love parades and are in the holiday spirit, be sure to join in welcoming Santa and Mrs. Claus as they join our Christmas Parade! After the Parade, come over to the old fire station behind City Hall to enjoy Cookies and Milk with Santa and tell him what you want for Christmas!

See acclaimed musical theater historian and storyteller Charles Troy whose shows have been embraced by audiences nationwide since 2006, and combine scans of rare photos, original graphics, edited audio tracks and video clips, live performers and a scripted narrative.

Join us for a special Sing Along at the Opera House! With all the lyrics on screen, you’ll be able to dream of a White Christmas right alongside Bing Crosby and Rosemary Clooney in the beloved 1954 film.

In this classic film, two popular song-and-dance duos - Wallace & Davis and The Haynes Sisters - fall in love while helping an old friend save his Vermont lodge. Sing along with Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen at these special screenings of this beloved Christmas classic.

All ladies are invited to stroll, shop, eat, drink, and enjoy holiday caroling and lights with friends on the historic Woodstock Square at Ladies Nite Out on Thursday, November 29 from 5-9 pm. While Ladies Nite Out is a free event, VIP packages, which include everything from reserved parking spaces to a VIP reception, are available starting at $35. Click here to learn more and to purchase tickets.

New this year, each participating business will offer its own show of appreciation: visit each location to unmask what they have to offer. Take your map, purchase an event cup if you’d like to sip as you go, and explore our local businesses. Learn More Here!

Enjoy the magic of the holiday season as the Judith Svalander Dance Theatre transforms the Opera House stage into a realm of fantasy. Experience Clara’s magical and enchanting journey as Tchaikovsky’s world renowned music is brought to life through the talent and grace of Svalander’s ballet company.

Miracle on 34th Street (1947), stars Edmund Gwenn, Maureen O’Hara, John Payne & Natalie Wood. It tells a lovely holiday tale. When a nice old man who claims to be Santa Claus is institutionalized as insane, a young lawyer decides to defend him by arguing in court that he is the real thing.

Experience one of America's most beloved pianists, composers and Steinway Artist Robin Spielberg during Spirit of the Holidays Sing-Along! The Woodstock High School Madrigal singers, directed by Brian Jozwiak, will join Robin on stage to perform Christmas carols and other winter favorites.

Before the concert, get a free hot chocolate at Ethereal Confections starting at 6:00 PM (first 100 cups) then join the WHS Madrigals outside the Woodstock Opera House steps at 6:50 PM for a special pre-show performance!

Saturday, December 15 from 11am-2pmLoyola University Chicago Retreat and Ecology Campus (LUREC)

Holiday Time! Time to prepare the holiday cookies for giving and enjoying throughout the season. In this hands on class we will make an assortment of festive holiday cookies and finish class with an old fashioned cookie swap to take home to share. There will be lots of sampling along with coffee, wine and a little bubbly to sip.

Join us for an evening of festive music, stories and a whole bunch of holiday cheer! Come help us kick off a brand new 2nd Saturday Concert series at Stage Left Cafe. Featuring Music by Cassandra Vohs-Demann, Billy Seger, Carrie MacDonald, Ken Johnson, Suzy Schwartz, Angie Kells, Debra Anderson, Joe Pesz and Jim Seidel.

Tis the season to be jolly, joyous, and watch The Muppet Christmas Carol movie. The Muppets perform the classic Dickens holiday tale, with Kermit the Frog playing Bob Cratchit, the put-upon clerk of stingy Ebenezer Scrooge (Michael Caine). Other Muppets - Miss Piggy, Gonzo, Fozzie Bear and Sam the Eagle - weave in and out of the story, while Scrooge receives visits from spirits of three Christmases - past, present and future. They show him the error of his self-serving ways, but the miserable old man seems to be past any hope of redemption and happiness.

Chris Collins and Boulder Canyon are not an impersonation act, but seek to honor John Denver’s legacy with fresh energy and musical integrity. Collins and Boulder Canyon have toured the country together delighting audiences with their talent, warmth and humor. Collins and some of the original artists of Boulder Canyon met in Aspen, Colorado at the largest annual celebration of John Denver’s life and music.

Join us for an evening of classic holiday favorites presented by the Woodstock Holiday Brass Ensemble. Featuring members from various Brass groups from throughout the county including: CorCorps, the McHenry County Horn Choir, The St. Thomas Brass Quintet, the McHenry County College Brass Quintet and the Woodstock City Band. Enjoy the warmth and fanfare of these beautiful instruments and the talented musicians who play them as they bring the very best of the holiday spirit to the Opera House stage!

In an ongoing tribute to the great Ed Hall, four internationally acclaimed musicians will present an evening of entertaining arrangements for the guitar as well as popular holiday favorites on the Opera House stage. Ed Hall’s annual holiday tradition continues and is one you won’t want to miss!